Triethylamine → HCID 19898680, compound

HRID 1196562Notes

Reaction equation

HRID 1196562 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[Na].Cl.Cl[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[CH2:13][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123811,7-HeptanediolHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 5360545Sodium

Product 1

HCID 19898680HCID 19898680, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,7-Heptanediol (ex Lancaster) (1.7 g) was reacted with sodium (0.24 g) in toluene (50 ml) as in Stage A(ii). 2-Chloromethylquinoline hydrochloride (ex Aldrich) was added followed by triethylamine (0.7 ml). After heating under reflux for 6 hours, the reaction mixture was partitioned between water and diethyl ether and the organic phase washed with brine and dried. The crude material was purified by chromatography on silica (eluting with ether-hexane) to give 7-(2-quinolinylmethoxy)heptan-1-ol (0.43 g) which was used in Stage b.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 6 hours
  3. customthe reaction mixture was partitioned between water and diethyl ether
  4. washthe organic phase washed with brine
  5. customdried
  6. customThe crude material was purified by chromatography on silica (eluting with ether-hexane)

Sources & evidence

ORD record
ord-18a6a55b3384402b8389ceca493e72ce
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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